Taking a V Card

[viking8811]

I have plans tomorrow to meet up with a younger piggy/raunchy guy and take his anal virginity. Other then the usual take it slow and plenty of lube, is there anything else I should do? I want to make sure it’s good for him and he can keep my load in him as long as possible. Are there any positions that work best for first timers? My cock is 6 in long, average girth, with a downward curve. 
 

I can’t wait to be the first to breed his hole. 

[Whitebitchboy]

Yes eat that ass. 

[max2001]

I wasn't treated with the respect you are showing - I remember shifting around somewhat and found being laid almost flat was easier on myself, with a leg bend slightly. Doggy and missionary was tough..

[SFCumdog]

Let him sit on it so that he can take it at his own pace to begin with. I think most virgins fear that the top will just slam it in them with no regard for how its gonna feel. If you want him to come back for more, than let him do his thing till he's used to it.

[DNG999]

When I was introduced my top layed me on my side and essentially spoon me from behind, gradually entering me. It seemed the most comfortable position for me. One we maintained until my hole was fully trained. He was a good thick 7” so I couldn’t take him all in one sitting, but over a few sessions. Because of the gentle introduction I came back for more. This work for me.

[yoursinmine]

On 12/29/2024 at 2:45 PM, viking8811 said:

I have plans tomorrow to meet up with a younger piggy/raunchy guy and take his anal virginity. Other then the usual take it slow and plenty of lube, is there anything else I should do? I want to make sure it’s good for him and he can keep my load in him as long as possible. Are there any positions that work best for first timers? My cock is 6 in long, average girth, with a downward curve. 
 

I can’t wait to be the first to breed his hole. 

I am interested in how the experience is for you. Please report back. 

[nate88]

18 hours ago, DNG999 said:

When I was introduced my top layed me on my side and essentially spoon me from behind, gradually entering me. It seemed the most comfortable position for me.

This has been my experience with virgins and newer bottoms too - the spooning position is usually the most comfortable and relaxing for them. It also helps us maximise body contact and lets me kiss/breathe on their ears and neck.

Laying the bottom on his tummy is another favourite of mine for the same reason, but something about that position seems to need a bit more trust established first.

[RawBottom76]

I have a fuck buddy who has only been fucked 3 or 4 times in his entire life. He told me his cum hungry pussy was ready to take on my fat 7" cock. As an experienced bottom, I did everything to get him to relax. Ate him out, gently fingered his hole with 1 finger, then finally 2. 

He got on all fours, and I slowly pushed the head in until it was just past the outer ring. As I'm doing this, I'm asking him if he's OK, am I going to fast or slow, just making sure he's good for the next slow push. All the while communicating with him about his discomfort level, until I was pelvis deep in his virgin like hole. 

I could tell he wasn't comfortable, so I laid my entire body weight on his back, and slowly pushed him down onto his stomach with his ass tilted up at the right angle for some good fucking. 

Needless to say, he now wants a foursome with me and 2 other tops to use his cumhole as we please. 

Edited January 1 by RawBottom76

[Bokkierob]

Start off by showering together. Make him wash you, especially your cock and balls. You will get hard so he’ll get a good look at what you’re going to slide up his ass. You should tease his hole with your fingers and your helmet. No penetration at this stage, just get him used to having his asshole teased. Then I’d advise you to teach him how to clean out his hole. Douche his ass with warm water and get him good and clean. He’ll be more relaxed if there are no “accidents” Dry him off and make him dry you off. Take him to your bed and put him on his belly. Spread his legs and bury your face in his ass. Force your tongue inside him and eat him out - he will love this. Take your time and let him enjoy being tongue-fucked. Lube his hole really well and also lube your hard shaft. Mount him and press your helmet on his asshole. You will feel his ring on your helmet stopping you from entering him. Keep up gentle pressure, push a bit harder but not too much. You don’t want to force your hardon through his ring, you want his ring to gently give way over your cock. Eventually you will feel his ring relax and open for your cock. Only your helmet will be in his ass so don’t go any deeper. He will probably yelp when you penetrate his ring. Reassure him that’s is the hardest part over for him. Stay still for several minutes until he’s used to having his ring kept open by your cock. Tell him you’re going to give him another inch - then slide another inch of your cock into him. Never ask him what he wants, always tell him what you’re going to do. Remember, it’s his first time being fucked so you’re the teacher and he’s the student. Repeat sliding your cock in inch by inch until you’re balls deep. Tell him you’re all in and tell him how good it feels. Stay balls deep for several minutes, complimenting him, kissing him, stroking him and telling him how great a fuck he is. Now you can start fucking him. Gently - it’s his first time so you can’t pound his ass like you would some experienced cumdump. Pull out half way then slide back in deep firmly and strongly - but no hard thrusting. Keep this up until you shoot your load. Tell him you’re going to seed him then tell him when you’re cumming. Remember to grunt and moan when you cum and tell him that was the best fuck you’ve ever had - you want to make it a memorable experience for him. Stay inside him until you go soft. Slide out and then spend time spooning him and playing with his cock. You can also make him cum if he’d like that. 

[AirmaxUK]

3 hours ago, Bokkierob said:

Start off by showering together. Make him wash you, especially your cock and balls. You will get hard so he’ll get a good look at what you’re going to slide up his ass. You should tease his hole with your fingers and your helmet. No penetration at this stage, just get him used to having his asshole teased. Then I’d advise you to teach him how to clean out his hole. Douche his ass with warm water and get him good and clean. He’ll be more relaxed if there are no “accidents” Dry him off and make him dry you off. Take him to your bed and put him on his belly. Spread his legs and bury your face in his ass. Force your tongue inside him and eat him out - he will love this. Take your time and let him enjoy being tongue-fucked. Lube his hole really well and also lube your hard shaft. Mount him and press your helmet on his asshole. You will feel his ring on your helmet stopping you from entering him. Keep up gentle pressure, push a bit harder but not too much. You don’t want to force your hardon through his ring, you want his ring to gently give way over your cock. Eventually you will feel his ring relax and open for your cock. Only your helmet will be in his ass so don’t go any deeper. He will probably yelp when you penetrate his ring. Reassure him that’s is the hardest part over for him. Stay still for several minutes until he’s used to having his ring kept open by your cock. Tell him you’re going to give him another inch - then slide another inch of your cock into him. Never ask him what he wants, always tell him what you’re going to do. Remember, it’s his first time being fucked so you’re the teacher and he’s the student. Repeat sliding your cock in inch by inch until you’re balls deep. Tell him you’re all in and tell him how good it feels. Stay balls deep for several minutes, complimenting him, kissing him, stroking him and telling him how great a fuck he is. Now you can start fucking him. Gently - it’s his first time so you can’t pound his ass like you would some experienced cumdump. Pull out half way then slide back in deep firmly and strongly - but no hard thrusting. Keep this up until you shoot your load. Tell him you’re going to seed him then tell him when you’re cumming. Remember to grunt and moan when you cum and tell him that was the best fuck you’ve ever had - you want to make it a memorable experience for him. Stay inside him until you go soft. Slide out and then spend time spooning him and playing with his cock. You can also make him cum if he’d like that. 

Agree, and I'd add that playing sober means both will remember the experience and all its little details and nuances. You always remember your first. 

If he's inexperienced then take some time to explore each other's bodies.  You mentioned rimming already which is an awesome way to get a hole hungry... It wasn't until a good while after my first time that I discovered how sensitive my nipples are, and giving them a twist or pinch  also works wonders in unlocking the back door.

Not sure if we are allowed to mention poppers in this part of the forum, but if not, then moderators please remove this part: they are useful in moderation in  these situations but I'd only suggest as a last resort if things aren't opening up and relaxing enough. 

[nate88]

9 hours ago, Bokkierob said:

Lube his hole really well and also lube your hard shaft.

Sometimes we forget lubing inside is just as important as lubing outside, especially for first timers. And especially if he has douched because that process will remove the mucus/moisture the rectum usually has.

Take the time to finger him - it will help lube his insides and also help his muscles stretch, and help him adjust to the sensation of being penetrated. Some lube brands include nozzles which are almost like mini douches - buy lube like that so you can squirt lube inside him too, or find a lube injector on Amazon. It will help your cock stay lubed as you penetrate him deeper.

[RawBottom76]

On 1/2/2025 at 7:24 AM, Bokkierob said:

Start off by showering together. Make him wash you, especially your cock and balls. You will get hard so he’ll get a good look at what you’re going to slide up his ass. You should tease his hole with your fingers and your helmet. No penetration at this stage, just get him used to having his asshole teased. Then I’d advise you to teach him how to clean out his hole. Douche his ass with warm water and get him good and clean. He’ll be more relaxed if there are no “accidents” Dry him off and make him dry you off. Take him to your bed and put him on his belly. Spread his legs and bury your face in his ass. Force your tongue inside him and eat him out - he will love this. Take your time and let him enjoy being tongue-fucked. Lube his hole really well and also lube your hard shaft. Mount him and press your helmet on his asshole. You will feel his ring on your helmet stopping you from entering him. Keep up gentle pressure, push a bit harder but not too much. You don’t want to force your hardon through his ring, you want his ring to gently give way over your cock. Eventually you will feel his ring relax and open for your cock. Only your helmet will be in his ass so don’t go any deeper. He will probably yelp when you penetrate his ring. Reassure him that’s is the hardest part over for him. Stay still for several minutes until he’s used to having his ring kept open by your cock. Tell him you’re going to give him another inch - then slide another inch of your cock into him. Never ask him what he wants, always tell him what you’re going to do. Remember, it’s his first time being fucked so you’re the teacher and he’s the student. Repeat sliding your cock in inch by inch until you’re balls deep. Tell him you’re all in and tell him how good it feels. Stay balls deep for several minutes, complimenting him, kissing him, stroking him and telling him how great a fuck he is. Now you can start fucking him. Gently - it’s his first time so you can’t pound his ass like you would some experienced cumdump. Pull out half way then slide back in deep firmly and strongly - but no hard thrusting. Keep this up until you shoot your load. Tell him you’re going to seed him then tell him when you’re cumming. Remember to grunt and moan when you cum and tell him that was the best fuck you’ve ever had - you want to make it a memorable experience for him. Stay inside him until you go soft. Slide out and then spend time spooning him and playing with his cock. You can also make him cum if he’d like that. 

It went very well for us. He said there wasn't any pain with all my prep work on his hole. Gonna try and get together with him again so I can breed his tight hole again. He wants to be slutted out, so I might have to arrange for two of my fuck buddies to come over. And breed him. He'll get the breeding that he desires after. 

[Bokkierob]

On 1/5/2025 at 6:00 AM, RawBottom76 said:

It went very well for us. He said there wasn't any pain with all my prep work on his hole. Gonna try and get together with him again so I can breed his tight hole again. He wants to be slutted out, so I might have to arrange for two of my fuck buddies to come over. And breed him. He'll get the breeding that he desires after. 

Good man, glad to hear you prepared his asshole so you could enjoy his tight young hole. Remember to push his limits every time - it's the only way he'll learn. Next time work his ring until you're through but then thrust every inch of your shaft inside him - then start fucking him immediately.  He needs to be taught that you're fucking him for your pleasure. Report back when you've seeded him again.